Regioselective Synthesis of Novel Mono-Substituted D-lactose Fatty Acid Ester Derivatives

Author(s): Mina R. Narouz , Sameh E. Soliman , Rafik W. Bassily , Ramadan I. El-Sokkary , Adel Z. Nasr , Mina A. Nashed .

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 7 , 2013

Become EABM
Become Reviewer

Abstract:

Three regioisomers of lactose fatty acid monoesters at positions 3', 6' and 3 and other related compounds have been chemically synthesized. The 3'- and 6'-O-palmitoyl-D-lactose derivatives were prepared via the regioselective esterification at O-3' and O-6' of the dibutylstannylene derivatives obtained from benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-Obenzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1) and benzyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-Dgalactopyranosyl)-β-D-glucopyranoside (5), respectively, with the acid chloride, followed by hydrogenolysis of the benzyl groups. The 3-O-acyl-D-lactose derivatives were prepared via the regioselective esterification at O-3 of benzyl 2,6-di-Obenzyl- 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside (9) using DCC coupling method with the free acids, followed by selective removal of the 3',4'-O-isopropylidene group, and then hydrogenolysis of the benzyl groups.

Keywords: Carbohydrate fatty acid monoesters, regioisomeric lactose fatty acid esters, regioselective esterification and stannylene derivative.

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 10
ISSUE: 7
Year: 2013
Page: [502 - 509]
Pages: 8
DOI: 10.2174/15701786113109990018
Price: $58

Article Metrics

PDF: 12